biostudies-literatureCheong PHNIGMS NIH HHS1513-6https://www.ebi.ac.uk/biostudies/studies/S-EPMC3164362biostudies-literatureUnknown8(8)[reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.Organic lettersTorsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.PMC3164362R01 GM036700-27R01 GM036700Cheong PHDanishefsky SJYun HHouk KNfalseTorsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.[reaction: see text] The stereoselectivity of the key epoxidation step in the synthesis of guanacastepene A is shown to be controlled by torsional steering. In this particular epoxidation reaction, the transition structure energetic difference is enhanced by the great asynchronicity of the forming C-O bonds that intensifies the torsional interactions.2006-01-01T00:00:00Z2006 Apr2024-10-17T15:03:23.831Z2019-03-27T00:43:29ZS-EPMC31643621659709810.1021/ol052862g